题目内容：

He demanded answers to questions that one would hesitate to put to one's intimate friends

优质解答

这句话这样子你就清楚了：He demanded answers to questions,while one would hesitate to put THESE QUESTIONS to one's intimate friends.
中文意思就是：他想得到这些问题的答案,而每个人在将这些问题交给知己时自己都会再三犹豫.（言下之意是：他想得到答案的这些问题,会让知己很为难.）
愚见,仅供参考.